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The Stabilities of Meisenheimer Complexes. Part 38. Kinetic and Equilibrium Studies of the Reaction of 2,2',4,4',6,6'-Hexanitrostilbene with Aliphatic Amines in Dimethyl Sulphoxide

DOI: 10.1039/P29840001785

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1785 - 1792 (1984)

Update date:2022-08-22

Topics:

Authors:

Crampton, Michael R.Crampton, Michael R.

Routledge, Paul J.Routledge, Paul J.

Golding, PeterGolding, Peter

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Article abstract of DOI:10.1039/P29840001785

Kinetic and equilibrium data are reported for the reactions of 2,2',4,4',6,6'-hexanitrostilbene (HNS) with four aliphatic amines in dimethyl sulphoxide, and are compared with those for related aromatic nitro-compounds.With each amine the most rapid reaction involves ?-adduct formation by attack at the 3(3')-positions.With the primary amines, n-butylamine and benzylamine, isomerisation to the thermodynamically more stable 1(1')-adducts occurs.However, with the secondary amines piperidine and pyrrolidine, attack at the 1(1')-positions is not observed, and this is attributed to their high steric requirements.It is shown that the formation of ?-adducts may involve rate-limiting proton transfer from zwitterionic intermediates to amine.A slow reaction is observed between HNS and each amine and is likely to involve amine attack at the olefinic bond.

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